Weekend Extra Exercises (WEE) : Week 13

Submission Date: 25/2/2019 (Monday by 4.30pm)

Name:
PSPM 2015/2016
1. Acid catalyzed dehydration of 2-pentanol gives compound V and W. Compound V exhibits
geometrical isomerism. Ozonolysis of compound V produces Z and AA. Draw the
structures of V and W. Identify the major product and explain your answer. Draw
geometrical isomerism of V.

Write the mechanism for the dehydration of 2-pentanol. Draw the structures of Z and AA.
Write the reaction equation for the ozonolysis of V.

By using a suitable alkyl halide and Z or AA, show how 2-pentanol can be synthesised via
a Grignard reagent.
[20 marks]

2. (a) Compound BB is formed from the reaction of benzene with CH3CH2Cl in the
presence of AlCl3. Oxidation of BB with hot acidified solution of KMnO4 gives
CC. Treatment of CC with ethanol in the presence of traces of sulphuric acid
produces DD.

Name the type of reaction that converts benzene to BB. Suggest the structures of BB,
CC and DD. Write the reaction equations for the formation of BB and DD. Write
mechanism for the formation of BB.

(b) An alkyl bromide EE reacts with CH3CH2OH to give FF, whereas compound
CH3COOCH(CH3)CH2CH3 is formed when EE is treated with a nucleophile.
Dehydrohalogenation of EE produces GG which obeys Saytzeff’s rule.

Deduce the structures of EE, FF, GG and nucleophile. Write reaction equation
for all reactions involved.
[10 marks]